Reaktion #86032

Reaktionsgleichung

potassium carbonate

(R)-1-Benzyl ethyl 3-t-butyloxycarbonylamino-3-carbamoylsuccinate

hydrochloric acid

→

title compound

Ausbeute 90.0%

(R)-2-t-butyloxycarbonylamino-2-ethoxycarbonylsuccinimide

Ausbeute 90.0%

Lösungsmittel

water

acetone

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionthe mixture was extracted with ethyl acetate
2. 2
   WaschenThe extract was washed with saturated brine
3. 3
   Trocknendried over anhydrous magnesium sulfate
4. 4
   SonstigeThe solvent was evaporated under reduced pressure
5. 5
   Waschenthe residue was subjected to silica gel column chromatography, in which elution
6. 6
   Sonstigewas performed with n-hexane/ethyl acetate (1:1) for purification
7. 7
   Sonstigerecrystallized from ethyl acetate/n-hexane

Vorschrift

(R)-1-Benzyl ethyl 3-t-butyloxycarbonylamino-3-carbamoylsuccinate (550 mg) obtained in Example 20 was dissolved in acetone (11 mL) and water (6 mL), the solution was added with potassium carbonate (231 mg), the mixture was stirred for 5 hours, and poured with 1 mol/L hydrochloric acid, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and then dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was subjected to silica gel column chromatography, in which elution was performed with n-hexane/ethyl acetate (1:1) for purification, and then recrystallized from ethyl acetate/n-hexane to obtain the title compound (358 mg, yield: 90%) as colorless crystals. Optical rotation [α]D25 was −29.5° (c 0.50, ethanol).

Quelle